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F5126

Sigma-Aldrich

m-Fluoro-DL-phenylalanine

≥98%

Synonym(s):

3-Fluoro-DL-phenylalanine

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About This Item

Linear Formula:
FC6H4CH2CH(NH2)COOH
CAS Number:
456-88-2
Molecular Weight:
183.18
Beilstein:
2939807
EC Number:
220-104-1
MDL number:
MFCD00004273
UNSPSC Code:
12352209
PubChem Substance ID:
24894882
NACRES:
NA.26

product name

m-Fluoro-DL-phenylalanine,

Assay

≥98%

Quality Level

200

form

powder

color

white to off-white

mp

240-250 °C

application(s)

cell analysis
peptide synthesis

SMILES string

NC(Cc1cccc(F)c1)C(O)=O

InChI

1S/C9H10FNO2/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)

InChI key

VWHRYODZTDMVSS-UHFFFAOYSA-N

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Biochem/physiol Actions

m-Fluoro-DL-phenylalanine, a toxic antimetabolite, is a racemic mixture of a substituted (halogenated) benzoyl D and L phenylalanine with potential use in antiviral and antimicrobial drug development.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Monica N Kinde et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(48), 13762-13767 (2016-11-20)
Voltage-gated sodium channels (NaV) play an important role in general anesthesia. Electrophysiology measurements suggest that volatile anesthetics such as isoflurane inhibit NaV by stabilizing the inactivated state or altering the inactivation kinetics. Recent computational studies suggested the existence of multiple
T Ogawa et al.
European journal of nuclear medicine, 23(8), 889-895 (1996-08-01)
To elucidate the mechanism of large neutral amino acid (LNAA) transport in cerebral gliomas and to evaluate the clinical usefulness of positron emission tomography (PET) with fluorine-18 fluorophenylalanine (18F-Phe), we examined 18 patients with cerebral glioma using dynamic PET and
M J Fiske et al.
Journal of bacteriology, 154(2), 623-631 (1983-05-01)
Pseudomonas aeruginosa is representative of a large group of pseudomonad bacteria that possess coexisting alternative pathways to L-phenylalanine (as well as to L-tyrosine). These multiple flow routes to aromatic end products apparently account for the inordinate resistance of P. aeruginosa
M G Hinds et al.
The Biochemical journal, 287 ( Pt 2), 627-632 (1992-10-15)
A fluorine-containing analogue of the cyclic AMP (cAMP) receptor protein (CRP) from Escherichia coli was prepared by biosynthetic incorporation of 3-fluorophenylalanine (3-F-Phe). 19F n.m.r. studies on this protein have provided direct evidence for cAMP-induced conformational changes not only within the
W D Kingsbury et al.
Journal of medicinal chemistry, 26(12), 1725-1729 (1983-12-01)
A series of di- and tripeptides containing D- and L-m-fluorophenylalanine was prepared and tested in vitro for the ability to inhibit the growth of the yeast Candida albicans. The results demonstrate that peptides containing L-m-fluorophenylalanine inhibited the growth of C.
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